


Kinktober 2020

by UnconsciousCelestial



Category: Undertail - Fandom, Undertale
Genre: Kinks, Kinktober 2020, Lemon, Multi, NSFW, Reader Insert, Reader Is Not Frisk/Chara, Undertail
Language: English
Status: In-Progress
Published: 2020-09-17
Updated: 2020-10-30
Packaged: 2021-03-08 00:07:10
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 15
Words: 16,663
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26516434
Author URL: https://archiveofourown.org/users/UnconsciousCelestial/pseuds/UnconsciousCelestial
Summary: Kinktober 2020! xreader one shots based off of daily prompts. Please be mindful of tags 18+ only!
Relationships: Bara Sans/Reader, HT! Sans/Reader, Ink/Reader, MT! Sans/Reader, Nightmare! Sans/Reader, US! Sans/Reader, US! papyrus/reader
Comments: 81
Kudos: 129





	1. Introduction and Voting

**Author's Note:**

> I’ll preface each one shot with any trigger warnings if you need to avoid something! If it’s a kink you enjoy, but the trigger concerns you, let me know! Maybe I can post an omitted piece💚🧡

Okay SO! I have mentioned in the past that I am participating in Kinktober this year! I have my kink list ready to go, most will be neutral reader insert, & only one story will have slightly dub con (stalking and stranger sex but it’s actually role play). What I need from you is the characters you want to see!! Please keep your requests to community fandoms or creators that have given permission for writing undertail.  
You can request by the day, or if you’re ambitious give me names for every day! I also need a vote for the final day, Goldilocks or Little Red Riding Hood! So without further ado, here is the list! If I dont get any responses, Ill still participate I will just have to choose myself! <3  
 ~~Day 1: Gags & S/D ft. mirrors~~ Ink Sans  
 ~~Day 2: Exhibitionism/ Voyeurism & Latex ~~ US Sans, ft Nightmare & Error  
 ~~Day 3: Begging & Knife Play ~~ MT Sans  
 ~~Day 4: Sexting & Masturbation~~ SFP Pap  
 ~~Day 5: Sleepy Sex & Cock warming~~ US Pap  
 ~~Day 6: Stalking & Stranger Sex ft. roleplay~~ HT  
 ~~Day 7: Frottage & Thigh-fucking~~ Bara Classic  
 ~~Day 8: Blindfolds & Worshipping ft licking~~ Dream  
 ~~Day 9: Cunnilingus & Sex Demon~~ LT! Sans   
~~Day 10: WAM & Facial ft. lingerie~~ LT! Sans  
Day 11: Phone Sex and Toys  
 ~~Day 12: Orgy & Multiple Creampie~~ FS, and Fell  
 ~~Day 13: Daddy/Mommy & Impact Play~~ TBA  
 ~~Day 14: Tentacles & Somnophilia~~ HT Pap  
 ~~Day 15: Human Furniture & Humiliation~~ Nightmare & co  
 ~~Day 16: Fear Play, Collaring & Biting ~~ FS Sans  
 ~~Day 17: Dry Humping & Against A Wall ft. “accidental” nudes~~ UF! Papyrus   
~~Day 18: Pet Play & Praise~~ Bara UT! Sans  
 ~~Day 19: Micro/ Macro & Orgasm Denial ~~ Error  
 ~~Day 20: Aphrodisiacs & Seduction Ft Hair-pulling~~ HT! sans  
 ~~Day 21: Sensory Deprivation & Massage~~ SFR Pap  
 ~~Day 22: Size Difference & Minor Vore~~ HT!Sans  
 ~~Day 23: Inebriated Sex & Anal~~ FS Sans  
 ~~Day 24: Hate-fucking & Face-sitting ft. deepthroating ~~ UT! Papyrus (OH LORDY what have I gotten myself into)  
Day 25: Cuckolding & Female Ejaculation  
 ~~Day 26: Stockings, Shibari~~ US Pap  
Day 27: Scratching, Nipple Play & Groping  
Day 28: Glory Hole & Dirty Talk  
 ~~Day 29: Formal Wear, Stripping & Threesome~~ US!Sans & UF!Sans  
 ~~Day 30: Recording & Fucking Machine~~ Fresh!  
Day 31: PARODY! You choose- Goldilocks or red riding hood 


	2. Day 1: Ink Sans

**Notes for the Chapter:**

> AHHHH Half an hour to spare.  
> I mixed Canon and Fanon Ink Sans together I hope you don't mind! Also I realize this is probably a bit tame and shorter than I expected, I really tried though. I had so many ideas and it just went brrrrrrt when I went to write it.  
> Please let me know what you think<3

Gags & S/D ft. Mirrors

It had been an overwhelmingly long week, everyone and everything was getting on your nerves. You desperately needed a break. The only thing that kept you going was your friend Ink. He had been messaging you here and there all week, giving you words of encouragement just when you needed them. It wasn't always the best advice, (like “just murder them”) but, it still gave you a little boost of serotonin regardless. The two of you didn't get to hang out very often, but with your own busy schedule you didn't mind as much.

You had been home from work long enough to have just curled up on your couch with a good book, and your favourite warm drink, when your phone started ringing. Sighing audibly in mild annoyance you reached over to retrieve it from the sidetable, your mood lifting considerably seeing it was Ink calling. He very rarely called. His voice was eerily deep, not at all what you were used too.

“I'm coming over,” you heard him inform you, then there was an audible click.  
No time for you to respond, no time to say you weren't decent. Oh well screw it, you were in your 40's and not dealing with it today. If he wanted to just come over without warning then he was going to just have to deal with you in your pajamas. Its not like you were uncomfortable with him anyhow. You continued to read your novel, wistfully thinking of the protagonist caught in the arms of the villain turned romantic interest. You loved the power play dynamic, sure it was a bit tropey in the novel but it was still nice to think about. Your thoughts were interrupted by a loud **THUMP**. You looked up to briefly see Ink splayed across your living room floor, only to bounce up like nothing happened.  
  
You stifled a chuckle. “You okay there?”  
  
“Just peachy. What are you up too?” He slid over to the couch, plopping down beside you. You waved the novel in front of his face haphazardly, and he snatched it out of your hands. He scanned over the pages you were reading, his eyelights flickering from shape to shape as he concentrated. He suddenly got a mischievous look, and faced you.

“Do you want me to dominate you, right now?” He asked casually. It came out of nowhere and almost startled you, even though you were sort of used to how blunt he could be. Still, you felt your face flush. You couldn't lie, the thought had crossed your mind once or twice in the past but you _never_ expected it to actually happen.

“WHY WOULD YOU ASK THAT!?” You squawked and grabbed a pillow in an attempt to hide your face.  
He plucked the pillow from your grasp and set it down beside you.

“Well, I have time to kill and it sounds like fun. You had a rough week, and seems like you could use the relief as well. We get along without me even needing to feel anything which is nice, and I trust you. Do you trust me?”

You didn't even have to think about it. There was no reason for Ink to fear, or dislike you, and if he was bored he would just leave.  
  
“Yes, I trust you,” You nodded.  
  
“Well I would like your consent then, and just know you can revoke it at anytime. Do you have any safe words you'd like to use?”

“Uhm stoplight colours are fine, and yes...” you exhaled.

Ink leaned over into your bubble, his nasal ridge almost touching the tip of your nose.

“I need you to say it all y/n” he whispered. Already sort of drifting into subspace you almost squeaked at how close he was.

“I want you to dominate me... Ink” you breathed.  
  
He sat back almost comically fast, and proceeded to take two vials out of his bandolier. A pink one and a red one. He took a small sip of the red, and a larger sip of the pink, then put the vials back. Pulling something else out of a pocket, he redirected his gaze back to you, and smiled wickedly. You couldn't help the goosebumps that rushed over you, in anticipation.

“Go upstairs y/n, and wait for me on your bed,” he requested.  
  
Any other day you would have quipped back, but you had a feeling today was not that day. You nodded, and hurried up the stairs. Should you undress? He didn't say. You stripped down to your underwear and briefly observed yourself in the mirror. Rolling your eyes you turned the mirror around. You felt Ink's hand trail up your spine, and you shivered. You could feel him place something around your neck, you assumed it was a collar from the weight of it.  
  
“Turn it back, I want to see us in it later. Do not underestimate your beauty mon cherie, tonight you are mine” he breathed near your ear from behind you. Despite your insecurities wanting to disobey, his words sent heat straight to your core and you did as you were told. Hooking one of the collar rings on his finger, he gently turned you around to face him.  
  
“I wish to gag you, is that okay?” he asked, dangling a ball gag in his hands. Your eyes went wide, but you nodded.

“Take off your underwear and kneel on your bed” he instructed.  
  
You stripped down slowly, letting him watch you. Once you were naked, you went and knelt on your bed. As you awaited further instruction, you looked back to him. He had that distinct rainbow blush upon his nasal ridge, and you could see his tongue swirling around behind his teeth. You also noted that he had already removed the majority of his clothing, except for his white shirt and brown boxers. After appreciating the way you looked for a moment, he approached you determined. Grabbing the back of your head, he kissed you hard. You relented, melting into his grasp and let his tongue sweep past your teeth. You kissed him back like he was a lifeline, holding yourself up with one hand and reaching the other to the back of his skull. He clasped your hand on his skull and pulled it away gently.

“Open” Ink commanded.  
  
You obeyed, and he placed the ball gently inside your mouth, closing the belt around the back of your head. He pushed you on your back roughly, causing heat to start pooling in your abdomen. You adjusted your legs, and he grasped your wrists with one hand. Bringing them up over your head, Ink began to explore and touch you with his free hand. He grabbed at your chest, kneeding gently. Then he tugged roughly on one of your nipples, causing you to cry out around the gag and arch your chest further into his hand. His hand traveled further down, feeling your dampness.

“You've thought about this haven't you, about letting me have my way with you...” Ink chuckled deeply in your ear, and trailed his tongue down your neck and along your collarbone. You gasped, how the-?  
He nipped your collarbone gently, bringing your attention back to him as he started slowly rubbing at your apex. You arched into his hands again, causing him to grin at your reaction. Taking your nipple into his mouth he slid a finger inside you and you moaned at the feeling. You could feel the drool beginning to slide down the side of your face. He growled heatedly, pulling his head back to watch you start to come undone. He kissed down your neck, while inserting a second finger inside you. As Ink slid his fingers in and out he curved them just so, and it hit that spot inside you. His grasp on your wrists tightened and you felt yourself getting close.  
  
He leaned in close, nipping at your earlobe. “Come for me mon cheri, I want to paint the room with your emotions”

You spilled over, moaning into his temple. He flipped you over onto your hands and knees, and you could see him behind you in the mirror. You saw another flash of rainbow colour before he penetrated you, reaching around with one hand to grab at your collar and his other hand under you. You watched yourselves in the mirror as he started going faster, enjoying you. You began to see the beauty in what he saw; your perfect mouth framed around the rainbow ball, the drool escaping merely evidence of your pleasure. It turned you on even more.

He slowed and bent over you, to croon in your ear, “Do you see how beautiful you are to me mon fleur? Touch yourself for me, come onto my cock.”

He picked up the pace again, as you stroked yourself. You got closer and closer, and as Ink locked eyes with you in the mirror, the two of you came together. You both collapsed into a sweaty mess upon the bed, and Ink went and started a bath for the two of you. After removing the gag and the collar, he carried you to the bath and got in. The two of you cuddled for a short while, playing with each others hands. Before long it was just too much for Ink and he abruptly stood up, walked over to the toilet and puked. You chuckled, kinda feeling bad for the guy, but you couldn't help hoping next time you would be brave enough to be bratty.

**Notes for the Chapter:**

> Ink! Sans belongs to @Comyet on tumblr https://comyet.tumblr.com/post/132998265968/i-n-k-t-a-l-e


	3. Day 2: US! Sans, Nightmare, Error

**Notes for the Chapter:**

> Alrighty so quick explanation of why I wrote the way I did!  
> Latex kinks range from just enjoying the feel to full on sensory deprivation, (which I believe is another kink listed? Some kinks are just going to naturally overlap in these things). I have more knowledge of simply wearing latex, how it can make you feel sexy and sensual, or powerful or submissive. And well, 'write what you know.'   
> Second thing to explain: A few of you asked for different characters and I got them at like 5:00am my time. I didnt feel I had enough time to ask people for a second option (and I didnt know if they wanted a ship? I dont read a lot of ships except when also in harems [Bluexdust, killerxouter inkxerror] so I dont know much about their dynamics sorry TwT ) and well with Voyeurism you kinda need someone to watch right? Error doesn't get much satisfaction on page here, but hopefully another day he has some time with reader? XD

Day 2: Exhibitionism/Voyeurism & Latex

You had been roommates with Sans and his brother for a couple months now, and they had been nothing but courteous and respectful toward your personal space and belongings. They never asked where you worked, or the hours you kept, which is why you had felt comfortable leaving one of your latex work uniforms (logo and everything) on the drying rack one day. You had been busy, and forgotten to grab it before you left for work. You were now regretting this decision however, as the end of your shift grew near. Sans, adorable starry eyed Sans, strolled right through the front door in a latex version of his battle body. Bandanna, gloves, and all. You could not believe your eyes, as he walked straight over to the drink bar you and a co-worker were tending. You were still attempting to pick your jaw up off the floor so you let your co-worker serve him.

Once he had been served you snuck over and hissed at him, “What are you doing here Sans?!”

“Whatever Do You Mean Y/N?” he smirked, “Im Just Trying Out This New Outfit I Have. Not Many Places I Can Really Wear It, You Know?”

You had never heard this tone from Sans, you were so used to his exuberant loud self. It was different, but not in a bad way at all.

You stepped back a bit, exhaling. “Right, that makes sense I guess.”

“Besides, You've Kept This Side Of You Hidden So Well For An Impressive Amount Of Time. Who's To Say I Don't Have The Same Ability?” He grinned, tugging the cuff of a glove a little higher onto his arm.

You nodded slowly. That also made sense. You thought you caught him giving you a once over in your bodysuit and apron, but it could have been a trick of the light. You suddenly felt very self conscious. You only wore the latex bodysuit for work, but you had started to appreciate the feel the longer you worked here. But now, with Sans seeing you like this? It was definitely stirring some of your latent exhibitionism.

“So, are you here for a scene? Or just to watch?” you blurted out before you could stop yourself.   
  
Sans just chuckled and tapped the side of his nose, and for it affected you more than you cared to admit right now. His eyes went wide all of a sudden, then grinning mischievously he turned to you.

“May I give you a ride home tonight?” He asked, dragging his fingertips up your arm to tug a little on your apron.

You almost choked on air at the boldness, but you nodded.   
  
You grabbed your belongings and followed Sans out to his motorcycle, noting he had changed back into streetwear. After supplying you with an extra thick leather jacket and helmet, the two of you were off, with you holding onto his frame tightly. Little did you know, the two of you were being watched.

  
Once the two of you were home, you led him up to your room and sat down at your desk. He shut the door and locked it behind him. Hurriedly closing the distance he grabbed the back of your head and kissed you with a talent and fervor you hadn't expected at all.

“I. Want. You. To. Know. That There May. Or May Not Be Someone. Watching Me Y/N, But We Can Stop. If You Want To...” Sans breathed between kisses.   
Your thoughts skidded to a brief halt, holding your hand up to his chest to pause him as well.

“Is it your brother?” you pulled a bit of a grimace at him. You had nothing against Paps, but, it was Paps. He was brotherly and 100% platonic for you.   
  
He laughed heartily, “Stars no. Nobody you would know personally. Maybe by name or reference...” he paused, thinking for a moment.

You grabbed the collar of his shirt and pulled him close, kissing his nasal ridge softly.

“Then let them watch,” you whispered.

Sans growled low, and pushed you to the bed.

~~~~~~~~~~From the closet~~~~~~~~~~  
  
  


“What the f̸̰͚̲̈́̊u̵͓̇c̴̨̺͚̐̈́k̵̡̜̥̑̂̀̕ is the little perv doing now?” Error cursed, glitching irritably. The dark figure that had appeared beside him shrugged and put his hands in his pockets.   
  
“you're one to talk. You came to her closet, not his.” Nightmare smirked while peeking through the slats of the closet door. Error glitched, scrunching up and hiding his embarrassed blush in his scarf.

“Eugh. Why are you watching? This is nothing noteworthy I should j̵̥̑ṵ̷̄ş̷̮̿̈́t̴̺͇͑̈́ leave.” Error muttered in annoyance.  
  
Nightmare didn't respond, he was watching you and Sans and to be honest, he liked what he saw. You were currently arching your back in pleasure as Sans was licking and sucking you, and as your moans increased in volume his magic started to heat in his pelvis. He stepped away from Error, but continued to watch from the slats, giving in and touching himself through his pants.   
  
Error finally heard you and couldn't deny there was something about it that was riling his magic up as well. He peeked through the slats himself, just as you reached your climax and it caused him to glitch out and away in pleasure, leaving Nightmare alone. Nightmare continued to watch as Sans turned you around and smacked your ass a couple times, causing you to shudder and moan breathily. Nightmare pulled out his hard cock, and groaned out loud at the touch. Sans paused for a moment to look at you, and you just smiled and nodded affirmation. He slowly penetrated you, making you gasp as he hilted.   
~~~~~~  
  
You knew you heard a groan of pleasure from your closet, and fuck if it didn't just turn you on even more. Sans was fucking you hard and fast now, as you stroked yourself, the two of you getting closer and closer to the edge. You looked over to the closet again, and you locked gaze with a cyan eye peeking through the slats. The thought of whoever that was, watching you, touching themselves to you, made you cry out as you came. You felt Sans come inside you, and you heard similar noises from the closet. Once down from your high, you went and opened the closet to see cyan tinged black goop dripping down the inside of your closet door.   
  
Sans saw it too, and starting chuckling, rolling his eyes. “Goddamn. And They Judge Me For My Kinks? Assholes.”   
You would have to ask Sans about it later. After tidying up the two of you cuddled, falling asleep satisfied.

  
  


**Notes for the Chapter:**

> Disclaimer: This is 100% fanon nightmare
> 
> Error belongs to lover of piggies https://loverofpiggies.tumblr.com/  
> Nightmare belongs to Dream!tale creator Jokublog


	4. Day 3: MafiaTale Sans

**Notes for the Chapter:**

> So I'm a couple days late I know, I'm attempting to catch up. I was having a bit of trouble and some personal life things happened. You know how it is.  
> Anyway, I tried to include some fun flavour since I absolutely adore 1920's gangster talk, I hope you don't mind. I also a sucker for big guy in a pinstripe suit and suspenders with an aura of danger, so sue me XD  
> Also, please let me know if you like these!! feeling a little insecure about them I guess.
> 
> TW: Car Crash, Small amount of Violence (Death of a goon), Ropes, Knives

Day 3: Begging and Knife Play 

You had some idea of what you were getting into, agreeing to be datemates with Don Sans “Comic” Gaster, but you couldn't help it. It could have been something in the way in the way he swept you off your feet when you first met, or the way he was now gazing at you from across his desk. Whatever it was, he made you weak in the knees and ready to throw some of your morals out the window.

Currently Sans was on the phone, dealing with a negotiation gone sour. You were in your best outfit, waiting for him patiently in an office guest chair. The plan had been to have a nice night on the town, but as the minutes wore on it seemed like it was going to have to be rescheduled. Sans was beginning to look frustrated, and he was flicking his pocket knife open and shut repeatedly. The blade caught the light every time it was popped open, and it was mesmerizing. It gave Sans quite an intimidating aura; Dare you say almost dangerous, and to be quite fair it was intoxicating. You shivered, letting your imagination run wild. Catching your eye Sans grinned mischievously, clearly noticing the effect that he was having on you. Placing the phone down on the receiver, then gathering his jacket and hat, he beckoned you to follow him out of the office. You followed wordlessly.

“Sorry that took forever sweetheart, some dewdropper thought he could try and chisel paps and I. I'm gonna make it up to you though, you okay having dinner at the house? Papyrus is out tonight, so it will just be you and I.” Sans informed you, as the two of you got into the back of his personal cab.

“Honestly that sounds like just the cat's meow right now,” you smiled, leaning your head onto his shoulder and nodding off.  
  
  
You awoke to the terrifying screech of metal scraping metal and the smell of burnt rubber as the cab crashed into something. Your door was flung open and you were pulled out of the car by big goons in masks. Something hit you over the head hard, and you passed out. When you finally came to, you observed your surroundings warily. You seemed to be in a back room of a warehouse somewhere, flyers and notices all over corkboards and a thick metal desk. One of the goons was dozing in the chair at the desk. As you regained more of your consciousness, you felt ropes pulled tight along your wrists, chest, waist and legs. You struggled against them a little bit, to no avail.

“Oi! Bruno! Wakey Wakey ya sap” you called to the guy at the desk. He awoke with a scowl, clearly not happy with being woken. You really didn't care about that though. Even if you found yourself in a Chicago overcoat, if Sans was still alive and well justice would be served. But, you didn't know that yet.  
  
“Yah, you! I just want to know what happened to Sans,” you inquired. He rolled his eyes at you and shoved his hat over his face.

“Don't ignore me, you palooka!” 

The goon spoke through his hat, clearly agitated. “If he wasn' fine, we wouldn' still have ya. Now close ya head!”

Well that answered your question. If Sans was alive, then it wouldn't be long until you would be out of here. All you had to do was wait.  
It wasn't long before you heard guns and yelling from outside, and then silence. The door smashed open and you saw Sans and Papyrus. It only took one bone through the goons chest and it was done. Sans flicked open his pocket knife and cut through the rope tying you to the chair. When he got to your waist however, he sliced through the fabric and you gasped involuntarily. You hoped that he hadn't heard, but he slowed down when cutting the rope on your chest and wrists. He nodded at Papyrus and the two of you blinked out.

When you opened your eyes you were standing in the Gaster's living room, and your adrenaline started hitting its high. You grabbed Sans and hugged him close.

“Thank you, thank you! I knew you would have come, but still, thank you” you muffled into his collar.

He embraced you tightly and placed his teeth to your head, in a soft kiss. He pushed you away gently then, crouching down to check the damage he had done to your clothes. You felt your face flush, slightly embarrassed at the noise you had made earlier.

He looked back up at you questioningly, “I didn't hurt you, did I? I don't see a mark...?”

Oh. He thought he had hurt you!

“Ahhh no.. you didn't hurt me, I felt your chiv cut through the fabric and it surprised me that's all.”

He stood back up, and gazed at your now heated face, and recognition lit up his eyelights.

“Oh...ohhhhh, well then, how about we have a little fun then heh?” his grin turned mischievous, and he scooped you up and shortcut to his bedroom.

Standing in his room, he circled you with that devilish grin. He flicked out his pocket knife and you shivered in anticipation. Quick as a bullet he zoomed in close, and sliced through the fabric under your chest, exposing your midriff. You sucked in air and he continued this until you were essentially left in your underclothes. He pulled back to admire his handy-work, leaving you shaking with adrenaline. He was too far away, you needed touch him, to be touched.

“Sans, please...” you whispered, reaching out to him. He stepped back out of your reach, and disappeared.  
All of a sudden you felt the cool blade sliding down the back of your neck, gently down along your spine, eliciting a guttural moan from your throat. The heat in your face had shot down into your abdomen.

“What's that doll? I didn't quite catch that...” he chuckled low in your ear. You reached for him again, you grabbed air as he dodged. You felt the sharp blade drag lightly along your thighs, just under the dip of your buttocks.

“Sans, I need you,” you moaned, slipping to your knees. He lifted you back up, and brought you to the bed.  
Laying down beside you he spoke low in your ear. “Then beg”  
He lazily dragged the blade softly over your nipple, and down to circle your navel. Abandoning the blade, he dragged his fingertips along under your navel teasing you.

“Please Sans, I want you to touch me...” you gasped.

“I am touching you,” he chuckled in response, now dragging his fingertips along the inner of your thigh.

“I need to come...oh fuck... please let me come” you exhaled.  
  
With that Sans leaned over you and kissed you deeply, maneuvering his hand to stroke you, rubbing that bundle of nerves just so. He quickened his pace, and you felt yourself getting closer to the precipice. He nipped your bottom lip, gently tugging it and letting go. Letting his tongue hang out of his mouth slightly, he shifted lower and swirled his tongue around your nipple. The feelings combined crashed you over the edge and you cried out. When you had gained your breath, you shot up and pushed Sans down, undoing his belt.

“Your turn,” you smiled maniacally.

**Notes for the Chapter:**

> I actually dont know who created MafiaTale, and I did a bit of digging but still couldnt find an accurate answer. If someone knows, please let me know!


	5. Day 4: Sexting & Masturbation

**Notes for the Chapter:**

> Hopefully Ill be able to properly catch up, but for now here is Day 4! Its a bit short, so there is a bonus POV. It felt too clunky to put Rus's perspective in during the main part. *shrugs*  
> I had a bit of fun writing this one, I love late night walks and SFP Pap just reminds me so much of them.   
> Hope you enjoy~

Every step you took marked the beat of the song that was playing through your earbuds as you headed toward the harbour front. The night air was crisp and cool, but you were keeping cozy in one of your datemate's jackets. It was warm, and smelled like spices and his cigarettes. You pulled it close to you, inhaling deeply. It pulled on your heart, he had left for a couple of weeks with his brother on a trip and you missed him something awful. When you got to the harbour you hiked to the far end of a water break, and pulled out your phone waiting for 'Rus to text you to let you know he was alone. While you waited you just looked out to the horizon, daydreaming while listening to music. The stars were out in full force, the night sky reflecting on the calm water was giving you the illusion of being in a globe.

You felt your phone vibrate on your leg, and upon checking it, your hopes were confirmed. Rus was finally back at the hotel.

[Rus: hey im in my room]

The bats in your stomach were soaring.

[you: heya love, I'm at the waterfront. I miss you... I wish you were here. The sky is absolutely gorgeous. I hope you don't mind I borrowed your jacket...]

[Rus: I know, I wish I could be there too. Too tired to come back tonight tho. and honestly thats okay I love the way it looks on you]   
  
You smiled and nodded to yourself. You expected as much. You didn't mind so much when he had to leave, as long as he came back. You were a little pent up to be honest and were beginning to desperately crave his presence. You were not about to give him that extra boost to the ego though.

[You: Its ok, I understand. What you up too?]

[Rus: nm. What you wearing? ;)]

You laughed, you had expected a response like that. The two of you texted back and forth for a while, the texts getting progressively more and more flirtatious and filled with innuendos. The smooth talker that 'Rus was, you were also getting thoroughly turned on. Thinking about having a little fun, you glanced down the pier to make sure that no one else was around. There were a few people out on the docks, but they most likely wouldn't come out this far.

['Rus: Youre thinkin' about touching yourself, arent ya? Naughty. Absolutely no self control.]

You chuckled, shaking your head. How the heck did he know? You quickly typed out a retort.

[You: You're one to talk mr.! You probably already have your cock out :p]

You were being a little coy in text, but honestly thinking about 'Rus touching himself had you rubbing your thighs together, and biting your lower lip. You could feel the heat in your lower abdomen, and the urge to touch yourself was growing rapidly.

['Rus: tell me what you're doin right now]

He didn't deny it, and fuck that was hot. You proceeded to quickly type out what you were doing/going to do, and slipped your hand up under your shirt to play with your nipples. The cool air blew across them, causing you to gasp. You lifted your shirt up to expose them a bit more. You quickly read what he had replied with, how much he'd love to be there behind you, nibbling on your neck and making you squirm. How he'd love to be the one playing with you. You replied how much you wanted that too, how much you wanted to be there kissing every inch of him.   


You told him as you reached your hand down past the band of your underwear and started teasing yourself slowly. You pulled the hood of his jacket up over your head and laid back on the stone, reading his texts and picking up the pace of your rubbing. He told you how he wanted to be tasting you, making you cum with his tongue. Fuck... you were getting so close. You inhaled the scent of his jacket, reveling in the memory of his tongue on you. You told him as much, apparently he was reaching the edge as well.

[Rus: so close....come for me luv]

Getting a brilliant idea, you hit audio record. Shoving your knuckles in your mouth as you climaxed, You moaned around them in a pulsing and shaking mess. You hit send as you laid there in your afterglow, breathing in the soothing combination of lake air and Rus's scent. Your phone went off again, and you smiled deviously at the list of expletives. Oh you were so gonna get it when he got back.

~Bit short, so bonus POV!~  
  
Stars above, you were actually touching yourself out on the water-break. Rus couldn't believe how hot that was, how _naughty_! As soon as he had read that you were teasing your nipples, imagining it was him as the cool air stimulated them, his hands were freeing his already formed cock from his boxers. He laid down on the hotel bed and began stroking loosely at first, using his free hand to stroke various sensual spots in between texting you. He thought about how much he loved making you squirm, when hes nibbling on your neck and teasing you. He groaned at your replies, (your hand was now down your pants) and he quickened up the pace, bringing himself closer and closer. He started thinking about how badly he wanted to taste you, to watch you come undone for him. His let his tongue hang out over his jaw, not caring about the little bit of drool slipping out. Fuck...it turned him on immensely that you were practically rolling in his scent. He needed you to come now, he was so close. Then you sent the audio. He was confused at first, then when he played it, he heard you. You had just sent him an audio of your orgasm. He hastily resumed pumping his cock, replaying the audio twice before he too climaxed, the evidence now all over his hands. With his free hand, he sent an almost incoherent string of curses, completely unable to put to words what that had done to him. He grinned mischievously, he was going to do anything it took to hear you like that again.


	6. Day 5: US! Papyrus

**Notes for the Chapter:**

> Goddamn I thought that this was longer than it actually is. It sure felt like it T-T  
> I think I'm getting better? Now I just need to work on my length. teehee. dirty jokes.   
> Anyway, let me know what you think please!!

The morning sun was warm and bright, peeking its way through your curtains. You checked the time, rubbing your eyes groggily. It was still pretty early in the morning, and your day off to boot. Sighing contentedly you shimmied back into your datemate’s embrace, eager to get a little more sleepy cuddles. Stretch stirred slightly in his sleep, wrapping his arm around you. You were currently the little spoon, and you wriggled to fit in closer to the shape of his frame. Still a little uncomfortable, you wriggled a little more, trying to get your legs in just the right way. Stretch’s hand grabbed your hip and groaned sleepily.  
  
“Darlin, if you don’t stop moving like that, I’m gonna have a good time...”  
  
You froze instantly, face flushing with slight embarrassment in realization.   
  
“Ahhhh noooo, I’m sorry, here I’ll move...”  
You went to shift away, but his hand on your hip was firm in place.  
  
“I didn’t say I was bothered, did I? In the many ways to wake up, I certainly can’t complain about this one...” he assured you, his voice still low and gravelly from sleep. You relaxed, and let him pull you closer, your butt now firmly pressed into his pelvis.   
  
“There, see, much better...” he muttered in your ear, sending pleasurable shivers down your spine. Lazily he traced his fingertips down your thigh from your hip, and back up again. Every touch causing your nerves to tingle in anticipation.   
  
“Mmm, that feels nice,” you yawned, nestling into his touch.  
  
He responded by nipping your earlobe, and slipping his wandering hand up along your tummy and trailing around your navel. Moaning softly, you rotated your hips, causing your buttocks to grind into his now very hard cock. Stretch groaned into your ear, causing more goosebumps along your body. His one hand was now trailing along the waistband of your pajamas, slowly grazing the skin as he tugged them down along with your underwear. Using your knees and feet you shimmied them completely. Shifting slightly, you positioned yourself at a better angle to kiss him. It started out slow and sleepy, progressively getting more passionate as Stretch’s tongue entwined with yours. You felt him reach down and slowly start stroking you, while grinding up against your butt, and you moaned into his mouth. When you gasped for air he pulled back, lightly tugging your bottom lip with his teeth. You watched fixated as he slicked two fingers wet with his tongue, and gasped in pleasure when he slid them down and around your hole. After you were thoroughly lubricated he gently inserted a finger, and pumped softly.  
  
“Are you ready luv?” Stretch whispered in your ear.  
  
“Fuck, oh fuck yes...” you exhaled, and you felt the tip of him pushing slowly into you.   
You inhaled shakily, and pushed onto him until he was all the way in. He wrapped his arms around you, and slowly pumped, never fully pulling out. Every push was slow, but every pull was fast. Every time he hilted he pushed that spot inside of you just so, and along with stroking yourself you got closer and closer to reaching your climax.  
  
“Ahh, I’m gonna come...”  
  
“Unnnh me too luv, come with me” he breathed into your temple.   
You felt him pulsing and rattling into his own and it pushed you over into yours.   
The two of you cuddled a while, dozing off, too lazy and sleepy to bother removing his dick from you.   
  
When you awoke, you were a little confused at the pressure you were feeling in your abdomen, until you felt Stretch stir. His slight movements shooting pleasure down into your core reminding you that he was still inside you.   
  
“Well this may be an even better way to wake up,” he moaned behind you, pushing himself further into you again.   
  
Now fully awake, Stretch grabbed your hips and rolled until you were under him, doggy style. No complaints from you, as he made sure you were lubricated you again, then he began to fuck you rapidly. Nothing slow about it this time, the two of you needily chasing your climax. You came first, fast and hard which brought him to his as you pulsed and shook around him. The two of you collapsed into a heap, his weight on top of you soothing.   
  
“Mmm I love you Paps” you crooned, satisfied.  
“I love ya too darlin” he whispered, kissing your temple.   
  



	7. Day 6: HT! Sans

**Notes for the Chapter:**

> Oof. I dont even know how to explain this one. Again I had all these ideas and this is what came out.  
> I hope you like it, I'm trying not to get repetitive with wording.  
> TW: Stalking, SLIGHT dub con, but I think I made it obvious after a hot minute that it was roleplay.

Day 6: Stalking, Stranger Sex ft. Roleplay   
  
  
“So that’s when I told him stupidly, ‘No can dosville babydoll’” your friend cackled, finishing up her story about her most recent date.

“Oof...what a keeper,” you chuckled sarcastically.  
He had sounded like a complete tool, and obviously you were both glad that she had walked away from that many red flags.  
  
The two of you had met up later in afternoon, at one of your favourite local cafes.  
It was so nice catching up and chatting, ordering beverage after beverage, you ended up loosing track of time.  
It was nice though, you hadn’t been able to hang out in a while and you had been missing her.

“So! Tell me about your new, what...datemate you said?” she inquired, turning the attention around onto you, “You two are pretty serious huh? When do I get to meet them!?”

“Probably not for a while, they are pretty reclusive and don't get a long with other people very well...” you informed her.  
  
You knew the real reason but you weren't about to tell her that. You knew she cared about you, and that was exactly why you didn't dare; she'd completely freak out and kidnap you. Besides, you trusted them with you, because they liked you. Your datemate was working on socializing himself but you didn't want to push them.  
  
“Besides, its much nicer just hanging out the two of us for now,” you finger gunned, attempting to be silly and change the subject.  
  
She thankfully took the bait and went on reminiscing about the last time you hung out, and you exhaled in relief. It's not that you didn't want talk about your datemate, heck, you could word vomit about everything you liked about him. But some of the things you loved and appreciated were the things you didn't want to divulge just yet. They would lead to more questions, some you didn't even have answers for yourself. Better just to keep quiet, and hope that the little you could say would be good enough for now.  
  
As the sun began to set low in the sky, you began to feel like you were being watched. It was like a heavy blanket you couldn't remove. Looking around, no one seemed to be paying the two of you any attention. Outwardly you shook it off, trying not to give your friend any suspicion that something was bothering you. Inwardly, you were battling with trying assure yourself it was just some minor paranoia, and your instincts screaming at you to listen.  
  
The feeling did not dissipate as you said your goodbyes to your friend, and as you left the cafe it just grew stronger. You popped your headphones in, in an attempt to distract yourself. As you started your steady stroll home, the hair on the back of your neck started to rise and the chilly night air did not help. You were beginning to feel nervous, so you turned your music down a bit to gain some awareness. Every distant car screech or siren made you jump, and you were constantly looking around you. Then you saw a large shadowy figure about a block behind you. There is no way they were following you...right? There was a few other ways you could walk home, so you took a turn and continued on your way feeling a little relief. Then you felt that intense stare once more. You glanced behind you, and there was that figure again. You attempted to loose the figure twice more, and each time they caught up with you again. Starting to loose your flight mode, and leaning into fight mode, you grew frustrated and a little angry. Spotting a familiar dark alley, you ducked into it and hid behind a large garbage bin. You waited a few minutes, occasionally peeking around the bin, waiting for the figure to pass by. Minutes ticked on, and still nobody was passing by the alleyway. Exhaling in relief, you hopped up from your crouch. You stood up and brushed yourself off. Attempting to exit the alleyway however, a very large bone hand slipped over your mouth and dragged you back.  
  
Whoever held you captive growled low in your ear, “I wouldn't make any sudden movements or noises if I were you right now cinnamon bunny...”  
  
You nodded, swallowing your panic, and he stepped back. His large frame leaned up against the wall, and one large red eye casually looked you up and down. The powerful aura he exuded was strangely intoxicating, and his intense gaze was beginning to make you weak in the knees, for some explainable reason.

“Why were you stalking me?” you blurted.

You blinked and suddenly you were shoved up against the wall, his large frame towering over yours. He leaned down into your neck, inhaling deeply. The sensation tightened things low in your belly, and covered your skin with goosebumps. You softly caressed his cranium, careful to avoid the damage.  
  
“Isn't it obvious?” His deep baritone rumbled within your chest, surprisingly pleasurable. You weren't giving in this easily though.

“Why don't you enlighten me? I don't even know you, and here you are pinning me up against some alley wall. Buy me dinner first why don't you...” you retorted.  
  
His grin stretched wider, almost mischievous.

“heh. If you're hungry I have something you can eat,” he chuckled, pushing his body closer into yours, his innuendo obvious. Dont laugh. Dont laugh. Dont laugh.

“Oh do you now? Well good thing I'm famished...” you winked, and sunk down onto your knees.

You pulled down his shorts easily, revealing the formed magic. It was marbled blue and red and quite large. Grabbing his cock with your hand, you swirled your tongue around the tip teasing him. He groaned low as you took him into your mouth, as far as you could go. You slowly slid him out and back in a few times causing him to grab the back of your head to steady himself. You started bobbing faster, not caring about the drool that slipped down your chin. Every hushed moan he let go sent pleasure low in your abdomen, thoroughly turning you on. The next thing you knew, he was grasping at the waistband of your pants and tugging them down hard. Lifting you up against the wall, you felt his hard cock pushing into your entrance. He crushed his teeth against your mouth as he slipped in, and as you gasped in pleasure he pushed his tongue in to entwine with yours. He started out slow, letting you adjust to his size, before quickening his pace. As he fucked you, you angled yourself so he was hitting that spot inside you just so. You reached down to stroke yourself as well, continuing to kiss him, the two of you chasing your climax fast and hard. He relinquished your mouth to kiss down your face and neck, then biting down on your collarbone. You cried out in bliss, your orgasm hitting you hard and pulsing. He came immediately after, groaning out his own release inside you.

When you opened your eyes, you found yourself back in your own room. Removing yourself from him gently, you kissed his temple softly.

“We should do that more often Stranger, that was amazing,” you crooned.

Sans just nodded, nuzzling his head into your neck and embracing you close to him.

“mine” he exhaled, then proceeded to doze off.

  
  


**Notes for the Chapter:**

> Not Canon HT! Sans, but HT! Sans belongs to SourAppleStudios https://horrortale-comic.tumblr.com/


	8. Day 7: Bara UT! Sans

**Notes for the Chapter:**

> oh my stars y'all. This one just flowed outta me, I'm pretty dang proud of it I hope y'all like it.  
> Also, please dont hesitate to leave me comments if you like these! they motivate me to keep going<3  
> ALSO ALSO please vote for day 31. So far we're at Goldilocks parody-1 Little Red Riding Hood-0

Day 7: Frottage and Thigh Fucking

You didn’t mind taking the subway home from work most days, it gave you a chance to sit and zone out. Other days though it was a crowded hectic mess, and messed with your claustrophobia. It didn’t help that you were a shortcake so it’s not like you exactly had an easy time holding onto the loops or handles. If you couldn’t get a seat, this usually left you pushed up against one of the poles, holding on tightly and trying not to be obtrusive.

Unfortunately today was one of those days, the loading platform was packed. Huffing in annoyance, you put up your ‘please eff off’ vibe, popped in your headphones and headed to the end dock. Not many people were crowded there, so this would give you the chance to get at least a decent standing spot. You felt the hair on the back of your neck stand up and someone standing real close behind you. You stepped forward a little, upping your ‘please eff off’ vibe to ‘don’t fuck with me’ and hoped it worked. The personal bubble violator backed off a little, and you exhaled softly in relief. You were seriously hoping there was going to be no delays on the train today, the sooner you were home and on your couch the better.

The train arrived and you slipped on as quickly as you could, attempting to avoid the swarm of people that formed behind you. All the seats were taken, so you went to the back of the cab. You enjoyed the view out of the back, so grabbing the closest pole you directed your gaze to the large clear door. People started squishing in, but your view thankfully remained unobstructed. The train started and the jolt knocked someone into you... someone big. A low chuckling rumbled from behind, strong enough you nearly felt it inside your own diaphragm.

“Heh. Sorry kiddo, not used to riding on the subway just yet” a low baritone boomed behind you.

With your headphones still in, you more felt it then heard it. Turning your head around to peek past your hood, your eyes nearly popped out of your skull. You had to scan your eyes up, since a freakin giant of a skeleton monster was standing there. A lovely blue hue decorating above his nasal bridge. Was that...blush? Oh...maybe he felt bad for bumping into you.

Taking your headphone out you muttered, “no worries. Not a kid though.”

“Just a turn of phrase, but noted...” he shrugged, and put his free hand in his pocket.

You nodded and put your earbud back in, resuming your attention to the back door. You could make out guide lights and the occasional door, and started letting your imagination take over.

The train screeched to a halt, and again you felt him bump into you, but this time he did not pull back as quickly. You ignored it patiently, sometimes it took new train passengers a few times to get balanced. More people got aboard, and somehow he ended up being pressed right into you. You inhaled. He was practically standing over you, and it had your senses screaming. Peeking up, your suspicions were confirmed. His large skeletal hand was gripping the same pole you were, and he was quite obviously trying to look anywhere but down at you. You chuckled to yourself, he was harmless, so you resumed your daydreaming.   
The take off was softer this time, but because of his close proximity he still swayed into you causing more friction than you would have liked. You exhaled, trying to keep your patience. It wasn't his fault, people could be so damned pushy on these things.   
  
This happened a few more times, but each time the pressure was a little harder and the friction lingering. You chalked it up to paranoia it at first, but then you definitely felt it, hard and warm against the curve of your spine. No mistaking what that was, and he wasn’t moving away. You should have been outraged. If anybody else had done this, and you would have been initiating some violence. But for some reason, you found the idea that little ol’ you was turning this big guy on, extremely pleasing.  
The train screeched to a stop again, the jolt allowing him to push himself into you, practically rubbing himself on your spine. You flushed with heat, as your own arousal rose. Biting your lip, you inwardly groaned. Fuck this was hot. He inhaled deeply, and he growled low, the sound reverberating against your head. You shivered, the tension pooling in your abdomen. Then you got a brilliant, absolutely mischievous idea. Even if you couldn’t do anything here, you might be able to help out your new friend. Taking out an earbud, you waited for your cue. The train started, and as he pushed into you, you pushed back into him, shimmying your spine onto his cock. He stiffened, grabbing onto your shoulders. He pressed his mouth onto the top of your head and groaned into your skull as fresh warmth bloomed onto your back. You chuckled, you were glad for your black sweater today.

At the next stop, the people in the end seats left.

Your new friend spoke softly into the top of your head, “heh. thanks lil buddy. feel free to join me, and I’ll return the favour,” and he slid into the seat, taking up the whole thing.

Looking around you cautiously, the train-car had mostly cleared. You gathered your nerve and approached him, chewing on the tip of your thumb.

“Heya. Have a seat,” he winked, patting his wide sturdy femur.   
You took another look around, this area was pretty obstructed from view, so you bravely straddled him. He slid you forward, and placed his hands on your hips to help keep you sturdy.

“So what’s your name sweetheart?” He asked in hushed tones.

“Y/n... yours?” You replied coyly.

“Sans, Sans the Skeleton. You okay with this?” he grinned.

You smiled softly back and nodded, stars he was effing cute. Smiling wider, he gently rolled his hands over your hips and began rocking you. Any arousal that had cooled, came back in full force causing you to gasp. His thick femur felt wonderful under you, and you ground down onto him, closing your eyes. Gaining confidence, you started your own rocking, and Sans exhaled shakily as you moaned softly biting your bottom lip.

“Stars you’re gorgeous,” he whispered.

You responded silently by moving his one hand up to your chest, and in a moment of understanding he dragged his thumb over your nipple. You almost keeled forward in pleasure, your climax building fast. You flashed opened your eyes, and he caught your gaze in his own eye lights. Another hard shot of pleasure burst through you, and quickening your pace you came undone; falling into his chest shaking and panting.   
  
Sans chuckled softly, “so uh, you wanna come back to my place?”

Unable to trust your mouth to form words, You could only nod enthusiastically.


	9. Day 8: Dream Sans

**Notes for the Chapter:**

> Quick shout out to @adorible for giving me the idea for Dream last minute because dang I had no idea. <3 lifesaver  
> It was hard to write, as this sort of thing is pretty close to my heart, but in a small way this was cathartic.
> 
> TW: Negative thoughts, Self Hate

Day 8: Blindfold & Worship ft. Licking

The door slammed loudly behind you as you gripped your coat tight. You were so exhausted, you were tired of fighting, tired of being told how worthless you were. A born dreamer, you had so many ideas tumbling around in your mind and right now you hated them. You hated that you had never been good enough, there was always a flaw with every idea, you hated your body, you hated your personality and on and on your mind tumbled down. The tears streaming down your face you hiked to your favourite sanctuary. The stars were always in perfect view here, you could be free to daydream and be yourself. The stars didn’t judge you, but fuelled you. You got lost in your thoughts, the tears streaming down your face.

“Human? Are you okay?” A warm friendly voice echoed from out in the air. You spun around, wiping your face hurriedly, looking for the source.

“Who’s there!? Where are you??” You called out into the open field.

“A friend, I’ve known you for a long time dearest.” The voice rang back, startlingly familiar feeling and filling you with warmth.

You let it bloom in your chest, desperate for that feeling of positivity and compassion. Before it could totally envelope you, that small horrid voice in the back of your mind stopped it. You don’t deserve this, this isn’t real.

“Hello!”

You opened your eyes and couldn’t believe it. There was an actual skeleton standing there, alive, and trying to talk to you. Gasping and stepping back in shock, you tripped over your feet and he reached out to catch you. He pulled you close, and you blinked in disbelief. He was so warm, and you melted into him. It was weird, the more you stayed close to him, you really did feel like you knew him somehow.

“Who are you though? I know you, but I don’t? What is your name?” Your thoughts came pouring out of your mouth.

“You can call me Dream!”

~~~~~~~~~~~

You still remembered that night so vividly, it was the oddest and best thing to have ever happened to you. Dream hadn’t stayed, and some days you felt you’d imagine it, if it weren’t for the little wooden star he’d given you to remember him by. Anytime your thoughts took over for the worse, you’d turn it over in your hands and you’d feel better albeit a bit lonely. You’d see him in dreams occasionally, which only made sense to you, but in a way it made things worse. You couldn’t touch him, or hold his hands.

Then one day, you’d been fighting with your parent over the phone again. They were cutting down your career choice, and once again obliterating any sense of pride or confidence you had in yourself. Never good enough. But now it was worse. Hanging up, your thoughts turned nastier, and you couldn’t find your star. Of course Dream left you, who would want you? You’re so pathetic really. You actually thought he liked you? That he wanted to know you? That you were special? Nobody likes you, why would he?

Your heart and soul shattering, it felt like it was trying to escape your chest.

You jumped as your hand was encased by a skeletal one, warm and gentle.

“I want to do something for you, but you have to promise you‘ll listen to me. This way of thinking is breaking your beautiful soul, and we really can’t have that. I’ve grown quite fond of you, and it. Please let me show you?” Dream whispered in your ear. You nodded, looking up to his face. You blinked and when you opened your eyes, all you saw was stars. Like a perfect bubble, you were in the middle of a calm lake on a dock. Pure joy bubbled up inside of you, and Dream sighed in pleasure. He pulled out a blindfold from a satchel at his side.

“Again I ask, do you trust me?”

“Completely...” you hummed.

He placed the blindfold over your eyes and waved his hand in front of your eyes. You didn’t react, not being able to see anything. The voices were beginning to get louder again.

“No, stop. Listen to me my dreamer, feel me. Let my voice and touch drown them out.” Dream commanded.

You exhaled and focused on Dream. You felt tugging at your chest, and then you felt exposed.

“I’ve taken out your soul y/n, and it’s gorgeous. Your colours are so bright and strong, despite everything you’ve been through and all the cracks. You are so much more than ideas and your dreams and what you have to offer this world. Your thoughts can lie to you, your heart, your soul, your body, they’re all so lovely”

He gently pressed his teeth to your soul to emphasize his point, and a soft ripple of pleasure waved through you. Gasping at the sudden contact you were not prepared for, your attention was now definitely focused on him.

He chuckled. “Such a lovely sound. You are so lovely y/n. So smart, so creative, so you. You don’t owe anyone anything but day after day you try. You want others to be happy, but you neglect your own happiness. When was the last time you did something just for you?”

He was stroking your soul now, you couldn’t see it, but you could feel it. He wasn’t touching you directly, but wave after wave of soft bliss was pouring into your abdomen. You moaned out loud before you could stop yourself.

“I wish you could see how wonderful you are to me y/n, my dreamer. Never doubt that please, I beg of you...” he whispered, but it resounded in your mind as you felt strong stabs of pleasure licking at your core, bringing you closer and closer to the edge. Unbeknownst to you, Dream was now licking at your soul, drinking up the pleasure you were receiving. 

“So delicious, my dreamer. Can you feel me? Do you hear me?”

“Yes Dream..oh yes” you moaned, getting closer and closer.

He pulled off your blindfold, showing you your soul in the middle of this starlit bubble.

“Look how beautiful you are to me, how lovely and sweet your soul is” he purred, wrapping his tongue around it again, taking it into his mouth and gently sucking. Your climax hit you, bringing you to your knees in tears of rapture.

The image of him with your beautiful soul in his mouth, here in this amazing tranquil place, it will forever be ingrained in your mind.

**Notes for the Chapter:**

> Disclaimer this is 100% Fanon Dream  
> Canon Dream belongs to JokuBlog on tumblr.


	10. Day 9: Lust Sans

**Notes for the Chapter:**

> So I had a strong mental debate on this one, and if it doesnt suit your tastes I will totally write the other one after Kinktober is done. My other idea was that reader was actually a demon summoned to perform on Sans, so if you wanna see that one too, let me know ;P  
> Heads up, for the purpose of the kink, reader has labia and a clitoris.  
> ALSO please forgive me if this is horrid, I can relate to reader for some things and welllll yaaah, only really read about it folks *shrugs*

Day 9: Cunnilingus & Sex Demon   
  
  
  
Fed up and frustrated, you threw your recently purchased toy on the ground with a resounding floppy thud.

“‘Feels like a tongue!’ They said. ‘Better than the real thing’ They said. Tch. I wish I knew...” you huffed out loud.  
  
Stupid advertisements. Stupid Sans. Maybe the toy would work for someone who has had an orgasm from oral, or maybe you were doing it wrong. Rolling over onto your stomach you checked your phone. No new messages and no new matches. Figures. It was All Hallows’ Eve, and a lot of people were out at parties. You had gotten invited to some, but you had declined, opting to spend it at home. No trick or treaters came out to where you lived, and it was much nicer to be soaking in the moonlight and enjoying your night alone then being hit on and disappointed and unsatisfied. None of your past partners had ever been able to make you orgasm from oral, or they weren’t interested, and now that you were a single Pringle again you wanted to see if it was just you and your mind.

You’d read about it, watched it, and wished for it. You’d even openly discussed it with your friend Sans. He hadn’t told you much about the place he came from, but he was super knowledgeable in a lot of sexual topics and you trusted him completely. True that a lot of his knowledge was monster based, but since coming topside he’d done a lot of studying on human sexuality and health as well. You really believed he could have been a sex therapist if he wanted to, but he much preferred the science behind things, not actually dealing with people. He was actually one of your friends that recommended the oral sex toy, it ‘came’ highly rated. You hurt your sides laughing when he told you that one, but you went and ordered it anyway. And now you were here, unsatisfied, and messaging him. Typing up a quick text, you hoped he wasn’t with a date.

[You: hey sex demon. You lied. 😑🤪]

It was a funny nickname with a funny inside story, but if he had a date they may not appreciate it. Ah well too late now.

[Sans: really? It didn’t work? Are you sure you used it properly? ...]

[you: oh, so it wasn’t supposed to go on my head? Dang, maybe I shouldn’t have thrown out the instructions.🤷♀️😩]

[Sans: heh heh. You alone tonight?]

[you: yeh. You?]

[Sans: At a party with some friends but I can come over if you wanna hang out?]

[you: nah don’t worry yourself. Probably gonna watch some cheesy movies or something, ttyl?]

[Sans: sure]

You rolled your eyes, that was probably the best you were gonna get from him tonight, once he started using one word texts he was on a mission.

You washed up and pulled on a robe, then made your way downstairs to your couch. Grabbing some snacks from your stash you curled up and flipped on the tv. Somewhere between Hocus Pocus and Legend you had fallen asleep. When you awoke, there was a dark figure in front of your tv. In a panic, you started throwing your snacks and pillows at the figure, and bolted to your well lit stairwell. He blipped in front of you, and you were able to see it was a skeleton, eerily similar to sans. This creature that stood before you however had beautiful purple and blue horns protruding on either side of their frontal, and was clad in all black. Tight black slacks, black dress shirt opened to the sternum, and polished black boots. Well if he didn’t just look like something out of one of the fantasy novels you read. Your already lust heightened brain nearly drooled at the sight of him, until you remembered that he was still in fact a stranger in your house. You spun around, to dash back down the stairs, and there he was again.

“Keep trying Flower, we’ve got all night.” He chuckled low, sending shivers down your spine.

You frowned in defiance. “I don’t know how you got in here mister demon, but I don’t know why you’re here and I definitely didn’t summon you, so, be gone!” You motioned shooing him.

He just cackled.

"Did you really expect that to work?"

"No. But it was worth a try," you huffed. "Seriously though, who are you?"

"For right now, that doesn't matter. You can call me whatever you wish. I am here to aid your needs"  
  


You sat there blinking at him for a moment, what the fuck does that mean? As your lust fueled brain filled it in for you, your eyes widened. 

"What makes you think YOU'LL be able to help me with any, ah, needs I have?" you inquired, staring him down.

"Does that really matter? If I can, I can. If I can't, then I can't." He grinned devilishly, and approached you with his hand out. "So what do you say?"  
  
"Well, I don't have any other plans tonight. Why not..." You reached out to put your hand in his cautiously, but he pulled back.  
  
"Nuh uh. You have to say it. Do you want me?"  
  
"Damnit...okay fine. yes. I want your help." you grumbled exasperatedly.   
  
He took your hand, and the two of you blipped onto your bed. He was on top of you, looking down at you with a familiar soft adoration. You shook your head to rid yourself of the image, and leaned up to kiss him boldly. He gladly met your mouth with his own, and as you parted your mouth he tangled his long tongue with yours. He kissed you passionately for a few moments, before trailing his kisses down your mandible and neck. You sighed in relaxation, it certainly felt lovely. He kept his attention on you, slowly trailing his kisses down your clavicle, and pulling open your robe to take your nipple into his mouth. He rolled it around and tugged gently with his teeth, eliciting a moan out of you. All the sexual tension you had given yourself earlier was coming back strong, the heat in your core building quickly. The demon continued his onslaught, kissing and nipping down to around your navel and waistline, teasing you and causing you to arch your back. 

"So eager Flower? I haven't even started yet...I can't wait to taste you" he smirked wickedly.  
  
You gasped in pleasure as he nipped your thigh, licking over the bite. Repeating on the other side, making you gasp and arch again.  
Next thing you knew, his tongue was flat on your mound, slowly dragging up, teasing. He did this a few times before spreading you, and inserting and retracting his tongue slowly. Every so often, he would flick upwards onto your clit. It felt wonderful, but you kept looking down at him, for any sign that he didn't actually want to be there. 

"You taste lovely sweet pea, just lay back, let me take care of you, feel me."  
  
  
Then he took it into his mouth and sucked gently, you cried out in pleasure, grabbing onto the mattress. The demon circled it with his tongue, before taking your clit into his mouth once again, bringing you so close to climax. He shoved his tongue into you as deep as he could, and retracting, took your clit into his mouth one last time. Your orgasm came crashing into you as the demon continued licking, extending the waves of pleasure rippling through you.   
  
"That, that was amazing, thank you," you exhaled, satisfaction bringing sleepy incoherent strings of thought. Sans just lay beside you, curling into you and holding you close. Kissing the top of your head he whispered,  
  


"You're welcome, my Sweet Pea"

**Notes for the Chapter:**

> Original Lusttale belongs to NSFWShamecave.
> 
> HOWEVER I do want to shout out a new lusttale au where Sans is Asexual and I think its absolutely lovely and you should check it out!! (@zirkkun both here & tumblr)  
> And also @Bigoltrashpile because they actually have sexy sexy skeleton demons<3


	11. Day 10: LT! Sans

**Notes for the Chapter:**

> Aaaah I hate falling behind but got lots going on here. Anyway couldn’t think of what to write for what was originally day 10, so switched it with day 11. LT! sans again!
> 
> Tw: messy, food sensory descriptions,

Day 10: WAM & Facial ft lingerie 

The fluorescent lights were bright and accusing as you walked down the baking aisle. Logically you knew that no one knew what you were planning on doing with the 10 large containers of vanilla pudding, a clear plastic tarp, but you still felt like everyone was staring at you regardless. You were just glad you ordered the small inflatable pool online.

Waiting in the checkout line, your thoughts drifted back to the other day when you came across some files your roommate Sans had left his laptop out on the dining room table. He was getting a drink from the kitchen when you walked past, and on his screen was an interesting article and pictures of sensual people covered in various messy things. It was so intriguing, you hurried to your room to do your own research, leading to you now standing in the checkout line trying to not be seem suspicious. 

“So what is all this pudding for?” The cashier piped up. 

“party...pudding cake” you sputtered, fighting your urge to run and hide.

The cashier just nodded, “cool cool, have fun”.

You bit your tongue, the urge to retort ‘Oh I intend to’ was too tempting. You paid, and got the hell out of there. 

The lights of your shared house were off, which was sort of to be expected but still a relief nonetheless. Sans was off visiting his brother for the weekend, and it gave you the courage and time to finally explore your new found interests. He was a good friend to you, and logically given his history he wouldn’t judge you. However, the huge crush you had on him was louder and this was a rather awkward scenario to be caught up in by someone you adore. Better to just indulge by yourself you thought.

The seven large bowls of dyed purple pudding made and setting, you went to prepare the rest of your space. Your bedroom would have been too small for the pool, and you hadn’t wanted to clog the tub with pudding. The living room would have to do, hence the tarp. Making sure that all the doors were locked, and the curtains closed tight, you went about the rest of the prep. Furniture was moved, the pool was inflated and placed on the tarp. Turning your phone off, and setting some mood lighting and music, you went to get yourself ready. 

You had dressed yourself in some comfortable sexy booty shorts, purple thigh highs and blue garter belt, and you were decidedly topless. Fetching the pudding, you poured two bowls into the pool, and set the other five down beside. The pudding was a little cool and squishy underneath your toes, it felt nice. You knelt down into it and slid your legs around, feeling the slickness coat your calves through the stockings. You slid down onto your stomach, letting the pudding squish between your fingers and squelch under your tummy. As a tactile person you were a little worried you’d get grossed out but this felt incredibly nice, taboo and freeing. You rolled around on your stomach a little, revelling in the colour and how the pudding coated your skin and lingerie. 

Your thoughts began to turn naughty, (you had specifically dyed the pudding purple as it was the colour of Sans Magic) and now you were wondering if his semen was also this purple...does it taste sweet like pudding? You sat up and grabbed a bowl, pouring it slowly onto your chest, watching the lovely purple globs slide down and drip into the pool. As your lustful thoughts continued, your lower abdomen started to heat and coil. You poured another bowl over your chest, this time dragging your fingers through it and dropping a few of the globs into your mouth. You sucked the rest off your fingers sensually savouring the vanilla sweetness.

“Stars above what are you doing y/n!?” 

You shot down into the pool in an attempt to hide you semi nakedness. Peeking up a smidgeon you saw Sans where he thought the couch would have been, with an extremely confused look on his face, albeit intrigued. 

“Uhm, What are YOU doing home? You were supposed to be gone all weekend!” You retorted. 

He was now observing you in your scenario, recognition clear on his face, a smug smirk plastered to his face. Oh fuck.

“Go ahead. Let it out!” You laid back down into the pool, preparing yourself for the oncoming onslaught. 

He leaned over the pool, and stuck a metacarpal in, swirling it around. 

“Heh. Didn’t know you weren’t so vanilla after all...I should be dubbed a saint puddin’ up with this...” he chuckled. You watched entranced as he licked the pudding off, then grabbed one of the remaining three bowls. 

“You never did mind getting dumped on” he finished, dumping the bowl down your body. 

His eye lights wandered, taking you in from head to toe. 

“Fucking hell you’re a messy flower now aren’t ya? Covered in purple goo. fuck, this is incredibly hot y/n” he leaned in close to your face, his voice husky and low. “Is it purple, because of me?” 

You nodded, embarrassed, hiding your face under crossed arms. 

“Sit up.” He commanded. You shivered, and obeyed. He took another bowl, and slowly poured it over your head, watching intensely as it poured down your face and hair, dropping on your chest. 

He inhaled sharply, “are you turned on by this y/n? Does being messy get you all hot and bothered? Because I have to tell you, seeing you like this, covered in purple gunge, fuck it’s so incredibly sexy. Can I join you?” 

You could hardly believe your ears, not only did Sans find you sexy, but he wanted to join you. 

“Yes Sans, if you’d like”

He took off his jacket and slid in clothes and all, and handed you the last bowl. You slowly poured it over him and he shivered, as the pudding slid down his skull and onto his crop top and ribs. You gasped, fuck he was so incredibly attractive. Next thing you knew, you were on your back, Sans on top of you, pushing his teeth into your mouth. The pressure forcing you to open your mouth, he shoved his tongue into yours, entwining it around. He pulled away from you, eliciting a soft whine. You wanted more of him. He stood up, looking down on you. 

“Stars y/n, I want to cum on your face, I want to cover you with my magic for real.”

Your cheeks burned, you were more than okay with this, as the tension inside you wound tighter at his words. 

“Yes Sans, please, cover me in your cum...”

That being all the permission he needed, He didn’t hesitate. In moments his hard cock was free, a lovely purple colour.

“Kneel” he demanded, and you sat up, kneeling at his feet. 

He rubbed and tugged slowly at first, just gazing at you. Needing your own release, you reached down and rubbed yourself through the underwear. He exhaled shakily, and sped up his own tugging, now pumping his cock directly in your face. You darted your tongue out to lick the tip and he almost buckled, his reaction causing you to increase your own speed. You licked him again, slowly this time, savouring the flavour. Not vanilla, but definitely sweet. 

“Fuck y/n, I’m gonna ...” 

He pumped vigorously, shooting loads of his purple cum all over your face. Feeling the rivulets drip down your face and mixing with the pudding brought you to your own end. You moaned loudly, shaking and doubling over in pleasure. Sans dropped to his knees, and kissed your head softly.

“Let’s go get cleaned up sweet pea” he whispered, and lifting you, he blipped you both to the bath.


	12. Day 11: Classic or whomever you wish to imagine

**Notes for the Chapter:**

> AAAAHAHHAHAHAH this was so hard to write. I dont know why, every time I went to write it I was deleting everything and just staring at the screen. I had a few suggestions for who to pick, but ultimately I went with Classic. I just couldn't see anyone else except for Red (And Epic! or Ink! but they're hard to write too) SO Even though I wrote it as Classic, Please envision whichever Sans you feel this would work for.  
> Please forgive me im trash and this is trash. kahsnberjsbjksbdjbf

Day 11: Phone Sex and toys

A hurried rapping on your storm door broke your attention from the novel you had been reading, and you frowned. You weren't expecting anyone today, and you lived by yourself. Annoyed, you made your way to the door, swinging it open to discover a package at your feet. It was definitely addressed to you, but you didn't remember ordering anything? You shrugged and brought it inside.

The package sat on your coffee table for the day, and by the time it was getting dark your curiousity had peaked. Grabbing a pair of scissors you slid it through the tape and tore open the box. There was a pretty galactic bag, and underneath was a beautiful starry purple & blue vibrator. You just about dropped the box in shock, then broke down in laughter. That little shit. He actually bought and sent it. That was the last time you divulged any of your 'personal' interests to your best buddy Sans. He was such a jokester, you really should have seen this coming. You shot him a quick text.

[You: You butt!! This thing is expensive, the laugh better have been worth it.]

[Snas: i dunno what youre talkin' about ¯\\_(ツ)_/¯ ]

[You: Sure sure. Srsly though, whyyyyyyy]

[Snas: cuz you said you wanted it]

[You: siggggggh you're still a butt]

By the end of the week you were tired, frustrated, and needed some you time. The toy had sat on your coffee table the entire week, and now it was practically calling your name.  
“Well, it would be a shame to not use it as intended...” you thought out loud, grabbing the toy and headed to the kitchen to sanitize it.

Some time later, you were up in your room reading some of your favourite fiction, warming yourself up. Your hands trailed down your body, teasing all your pleasure spots, finally reaching your pubis. You began stroking yourself softly, you wanted to make this last.

“Spooky Scary Skeletons, Send shivers down your spine....”

Sans was calling you. You immediately picked up, fearing something wrong. Very rarely did he ever call.

“Sans!? Are you okay!!”

“yeah, why?”  
you exhaled the breath you were holding.

“Goddamnit Sans, scared me. You hardly call! Thought something bad was happening. You're seriously okay? Paps okay?”

“yep. Just wondering what you're up too. Been thinkin about you.”  
Your eyebrows perked up, what? Where was this coming from?

“Oh? Uhm, thats sweet...” you paused, and looked down at your body, the heat rushing to your face. “Im uhm in bed relaxing.”  
At least it was partial truth.

“oh really? Relaxing huh?” he chuckled.

“YES. Relaxing.” You practically shouted, attempting to deny the accusation.

“heh. Are you making friends with the galaxy?”  
Your hand flew to your face and you groaned.

“Saaaaaaans. For your information, no I'm not.”

“You should...right now”  
You choked on air. Did you just hear him right? All your senses were screaming. Sure you've been harbouring a secret crush for years, but all the more reason to try and make sure you didnt mishear him. Wishful thinking and all that.  
“Pardon?!?”

“You heard me. I want to hear you.” he practically purred, his voice dropping like ten octaves.

“I just...why?” you blinked in disbelief.  
His chuckling sent shivers down your body, and heat straight to your core.

“cuz. Like I said, i've been thinking about you. Ive been thinking about you touching yourself, knowing I bought that toy for you. Imagining the sounds you would make, saying my name...”  
The way he was talking had your hand unconsciously reaching down to resume its previous task.  
“fuck...” you hissed, “Sans, I never knew, I didn't think...I thought it was a joke”

“heh. I could see that. But I just enjoy sending you good vibes”

“pfft.. dork. So... out of curiousity what else have you thought about me?”

“you're touching yourself right now arent you...?”

“yes...are you?”

“Stars, yes. I've imagined exploring you, finding out what makes you gasp and moan...what makes you shake. I want to taste you, mark you”

“To be honest, same.” You turned on your vibrator, and applied some lubrication.

“Shit, you turned it on didn't you...” he groaned.  
You teased your entrance, preparing yourself, then inserted it slowly.  
Inhaling sharply as the toy hilted you gasped, “Yes...its inside me now, ahhh fuck it feels so good”  
Sans growled into the phone, causing you to arch your back at the auditory delight. You could hear him grunting a little now, the speed of his pumping a little easier to hear. You worked yourself up to the pace, letting out your own moans ring out into the phone.  
“Unh I wish it was you fucking me right now...” you moaned.

“Fuck... you sound amazing, its going to be so hard to keep my hands to myself when I get back.”  
You just about died, the thought of him actually touching you, pushed you closer to your unraveling.

“Sans, I would love that, I swear....ohhh shit, I'm getting close.” You sped up your pace, angling yourself to reach that magic spot inside you.

“that's it, fuck yourself, I want to hear you cum. Say my name...” he growled into your ear, and you shook.  
Your climax hit you hard, and you called out his name. All you could hear from him now was grunting and erratic jerking. It wasn't long before he too was growling out your name.

You turned off the toy, slowly removing it. Cradling the phone in the crook of your neck, you took the toy to the bathroom sink and sprayed it with the cleanser.

“Hey Sans...”  
“yeah?”  
“thank you...”  
“heh, no problem. See you soon,” he purred.


	13. Day 12: FS & Fell Bros

**Summary for the Chapter:**

> Submissive Reader has their heart crushed, finds solace in Red, Boss, Slim and Vino.

**Notes for the Chapter:**

> Im SO behind Thank you for being patient with me! Im in the middle of finalizing a house purchase and its going to be a long distance move. (6 hrs!)  
> This one is longer than my others, I could have gone on and on seriously. ALL the Fells are a weakness for me I swear...  
> Just a note: I guess its more of a gangbang and less of an orgy since no fontcest or selfcest here, but I hope you like???  
> Anyway hope you enjoy! and please remember this is fiction (waves fingers, maaaagic), PLEASE PLEASE wear protection for your safety when hooking up with strangers!! <3<3
> 
> TW: Reader has self doubt feelings, breakup in the very beginning (dont worry fell bros rescue your poor lusty heart)

Day 12: Orgy & multiple creampie

The dripping faucet echoing in your skull marked the rhythm of your heartbeat as your partner told you it was over. They wanted to see other people, and you were just too clingy and submissive. They hated your indecisiveness and softness, it was driving them crazy. All you could do was nod as they took their bag and walked out the door. You slumped down on the floor and waited for your heart to still. Thoughts rushed through your mind, but the only bright beacon in your mind was Grillby’s. Grillby had a soft spot for you, his usual gruff asshole exterior had wavered towards you after you had helped him clean up after a particularly nasty bar fight.

Not wanting to be home, you quickly changed into some black jeans and a dark red sweater, before grabbing your keys wallet and phone. Slamming the door behind you, you headed to Grillby's.

You beelined to the bar, completely oblivious to anyone else around you. Sitting down on one of the stools, the most embarrassing sound echoing from your rear. You turned around mortified, pulling the whoopee cushion out from under you. Your mouth formed a perfect O, then you fell off your stool in a fit laughter. Someone caught you before you could hit the floor, and you froze. The immediate smell of mustard and smoky campfire infiltrated your senses. Opening your eyes, you looked into the face of a skeleton you sort of recognized. In was only for a moment, but you took in every inch of his terrifyingly intimidating yet handsome face.

“Heh. finally gotcha. I can’t believe it took this long to get ya to _crack”_ he grinned, his gold tooth glinting in the light.

You smiled softly, “yeah well not to _toot my own horn_ , but it didn't have to take much. I’m just sorely on edge tonight and have had enough of certain types of _assholes_. Needless to say, it broke me”

He chuckled, the other skeleton sitting beside him attempting to hiding his own grin.

You paused, finally registering what he had just said.

“Wait a minute... you’ve been waiting for a chance to prank me?”

“Heh yeah, ever since you walked your sweet ass in here the first time.”

You could hear a vague hissing from Grillby, as he came back to the bar front, clearly voicing his displeasure at this skeleton hitting on you.

“Heya Grillby, I actually came here to be cheered up, it’s okay. Can I get one of your magic drinks that will give me a little boost of serotonin? So and so left me tonight...” you grimaced.

Grillby’s flames burned a little larger and deeper purple, but brought you the drink you ordered.

Both skeletons were glancing over at you now, as you half chugged the drink placed in front of you. It wouldn’t take much to make you feel a little better.

“So tha names Red. This is Slim. You’re y/n, yah?”

You nod, and give a short wave to Slim. “I’ve always seen the two of you, but I’m often in my own mind, I’m sorry I haven’t introduced myself before...”

Red just shakes his head.

“Nothin wrong with mindin your own business, I’m certainly not gonna hold it against ya”

Slim pipes up, “nah. He’d rather hold something else against ya”

Red smacks slim on the back of the skull playfully.

“Ya boney butt, now they're gonna think we’re pervs”

“Not any more than I already had. Besides, nothing inherently wrong with that.” You grinned, than proceeded to gulp down the rest of your drink. 

You had relaxed considerably, and after some flirty friendly banter between Red, you, and Slim, you agreed to go back to their place to hang out some more. You assured Grillby you’d be fine, and you’d see him again soon.  
As soon as the three of you were out the door, they sandwiched you. You were completely flustered.

“Gonna take a shortcut, hold on tight.” Red commanded into your ear, eliciting a shiver down to your core.

“Onto what!?” You cried out, latching onto the first thing your fingers touched, as you were pulled into the void.

When you opened your eyes, you were standing in a cozy looking living room, which you naturally assumed was theirs. Your heart still racing, you leaned into the two of them for stabilization.

“Shoulda warned them Red, they look like a gryftrot in a flashlight,” Slim chuckled, lightly rubbing your arms in an attempt to soothe you.

“Yeah yeah it’s always freaky the first time,” Red shrugged, making his way to the couch and flipping on the tv.

He looked over at the two of you, “gonna stand there all night, or gonna come sit?”

You took the invitation and left Slim, sitting down a little ways from Red. Slim followed shortly behind.

“Scooch over will ya?” Slim smirked, wedging himself on the other side of you, pushing you closer to Red.

Normally you’d be cross legged or curled up, but currently your knees were pressed together to avoid being in anyone’s personal space. You were smooshed between two very attractive skeletons, and this realization was not aiding the sexual tension in the air at all. Trying to focus on the show became increasingly more difficult as Red put his arm around your shoulders, and Slim had his hand ever so slightly touching your thigh from where it was placed on his femur. It was at this particular moment, when the heat in your face was probably quite apparent, that two more skeletons walked in through the front door. A tall sharp looking skeleton headed straight for the kitchen, and the shorter of the two came over and stood in front of the tv.

“PUP! WHAT IS A HUMAN DOING ON OUR COUCH?” The skeleton growled at Slim.

You retreated into Red a little bit more, very unsure of the situation now.

“Just hanging out m’lord” Slim grinned lazily.

“That’s Vino, Slims bro. My bro, Boss, is in the kitchen,” Red whispered, dangerously close to your ear. You nodded, still apprehensive.

You felt him nip at the same ear, making you jump and gasp out loud.

Boss came into the living room at the moment, rolling his eyes. “SERIOUSLY RED?! YOU CANT EVEN GO TWO WEEKS CAN YOU?”

Red shrugged and grinned mischievously. “Sometimes it’s days, Boss”

Slim chuckled, and you smiled sheepishly. You were beginning to wonder what exactly you had you gotten yourself into.

“WELL, THEY ARE SORT OF ATTRACTIVE I GUESS,” Vino mused, looking you over.  
  
His intense scrutinizing was bringing out the submissive in you, causing you to squirm at the attention. Both Red and Slim felt your wriggling, Red just chuckled and Slims nasal ridge blossomed into a scarlet rust hue.

Boss scoffed, but his gaze also lingered a little too long.

After a few antagonizing moments, Vino spoke up.

“HUMAN, WHAT WOULD YOU SAY TO A LITTLE BIT OF FUN?” Vino proposed, strutting over and leaning over you.

You nodded, but he frowned softly at that.

“We’re gonna need a proper answer sweetcheeks,” Slim clarified, gently interlacing his fingers into yours.

“Oh! Aha, well then yes, okay. Wait, wait... do you mean with all of you..?” You checked, your lust addled brain wanting to be 100% sure you were understanding this correctly.

Slim leaned in real close to your other ear now, so both Red and Slim were practically sandwiching you again. 

“Mhmm...” Slim confirmed, inhaling at the crook of your neck, and at the same time Red nibbled your earlobe again.

“Ahhaa... oh my then yes definitely yes...” you groaned, your eyes practically rolling out of your head.

Now Vino was chuckling, and he lightly dragged a leather clad hand down your face, holding your chin in between his forefinger and thumb.

“I Can Sense You Desperately Need This, But I Want You To Know We Do Respect You And Your Boundaries. You Are Free To Say No At Anytime, To Anyone, And We Like To Use The Colour System With Our Play Dates. Do You Understand?”

You went to nod, and he held firm.

“Use Your Words Pet”

“Yes, I understand” you exhaled.

“GOOD!” He exclaimed, letting go of your chin in favour of reaching around and grabbing at the base of your skull.  
  
He leaned in and crushed his teeth against your lips until you parted them. He tentatively slid his tongue into your mouth, twirling it around tasting you, demanding your attention. All the while Vino was kissing you, Red and Slim had continued their onslaught. Slim was licking and nuzzling down your neck to your collar bone, while Red was nipping and licking down the same path along the other side. Slim guided your hand to stroke at the firm bulge that had formed in his lap, and you boldly reached your other hand over to Red’s lap. Both of them groaning and grunting in your ear at your touches had you practically melting in their touch.

You felt movement as Slim slipped down in between your legs, and the space was quickly replaced by Boss. As Slim worked on getting your pants undone, you stroked and pumped Red and Boss to the best of your ability. Vino was not relinquishing your mouth just yet. Once your pants were off, you were quickly manoeuvred onto all fours. Vino was immediately in front of you, his stiff cock almost touching your nose.

“Open Your Mouth Like A Good Little Slut,” Vino commanded, and you immediately parted your lips.  
Your mouth was invaded by the taste of him, as you did your best to take him all in. As Vino was using your mouth, Slim was prepping your hole. Red and Boss were looking on, Red’s eyes half lidded and his tongue rolling out of his mouth.

“I’m First Slim,” Boss warned him darkly, and he positioned himself behind you as Slim shimmied down to continue licking and sucking you intermittently. You whined at the quick loss of contact Slim was giving you, but let out a gutteral moan onto Vino as Boss pushed himself into you. Vino groaned, and grasped your head in his hands, gaining control again. Boss smacked your ass, and you drifted into a pleasurable subspace as your body was overwhelmed with sensations. Soon Boss was pumping his own orgasm into you, and Vino left your mouth. Red was immediately there, and you looked up dazed, slightly intimidated by his girth.

“Heh. I’ll go slow,” he winked, and you shivered in anticipation. You absolutely loved feeling used like this. As Red was guiding himself into your mouth, Vino grabbed onto your hips and eased himself into your hole. Slim was now rubbing himself on your soft stomach, and Boss was watching, his hands stroking himself into hardness again. You looked up into Red’s eyelights as Vino hilted, pulled out and slammed back into you. The sensation and connection had you spilling over into your orgasm, moaning and shaking. Red growled and gushed his own orgasm into your mouth, and Vino’s fast pace had him following shortly after. You felt his and Boss's magic drip out of you as he pulled out, the sensation of it extremely pleasurable.

“I Think You Should Help My Brother Now Pet,” Vino strongly suggested. You nodded and positioned yourself in between Slim’s legs.

“Where do you want to finish Slim?” You asked him gently.

“Your mouth...” he grinned.

You lowered yourself and took him into your mouth, eliciting a deep moan from him. You swirled your tongue around teasingly, and then bobbed until he was almost making you gag. It didn’t take long before he was unloading his climax into the back of your throat.

When you looked up, the other three skeletons were stroking themselves while watching you with intensity. It was going to be a long, fun night.

**Notes for the Chapter:**

> So thanks again for sticking around, I appreciate it!! Please dont hesitate to leave me comments, what you liked?? AND Please vote! Currently for day 31 Parody we are Goldilocks 1 and Little Red Riding Hood 1


	14. Day 13: UF! Sans

**Summary for the Chapter:**

> You’re tired, cranky and out of sorts. You decide to wake up a sleeping Red.

**Notes for the Chapter:**

> Soooo I’m totally 10 days behind. Please forgive me, I’m not in the right headspace what with moving soon🖤 I will do what I can to get most of these out before the 31! (I’ll still finish all the days)  
> Anyway, I totally believe Red is an ass man, and would love to be your daddy. So here.

Day 23: Daddy/Mommy & Impact Play

The mountain of laundry that needed to be folded was the last thing on your list of chores; and it was getting on your nerves. You were getting frustrated with the amount of chores that was being pushed onto you by your roommates. They were living here too, why the heck were you responsible for Red’s laundry. Fuck it, you were going to tell him to deal with his own goddamn clothes. 

Marching up to his bedroom door, you heard what you presumed was his snoring. Oh. He was never in a good mood when woken up... screw it. You were pissed and felt like stirring the pot a little bit, regardless of what the consequences may be.

You burst open the door, causing Red to give a shout and roll out of the bed. Okay that made you feel a little bit bad, but you couldn’t help the smirk that danced on your lips.

“Red! Why the eff am I responsible for all your freakin laundry!? I don’t mind pitching it in the wash, but I shouldn’t have to fold your shit too!” You barked at him, almost sounding a little like Boss.

He whipped his head to look at you, both eyelights glowing bright red, staring you down. The intensity of his glare began deflating you a little bit, and like a little reminder, the chain around your neck jingled as you stepped back. Oh shit. In your exhausted annoyed frame of mind, You had forgotten that folding his laundry actually was one of your specific chores. You had two choices ahead of you, continue down the path you were going and get in some real trouble, or apologize and hopefully get out of this relatively unpunished. 

You backed into the doorframe, “Ahhhh... I completely forgot...I’m sorry, I’m just super cranky and tired and I guess I needed to unload some tension...”

Red got up and sat down on his bed, his eyelights never leaving you.

“I ain’t happy about being woken up over something like this. If ya want to change the terms until you're working again that’s fine by me, but that ain’t the way to do it little one,” he growled.   


You shivered. 

“I know, I really am sorry, it wasn’t nice of me, like I said, I’m just tired and I just wanted-“

“-I don’t want your excuses. I get your frustrated but, again, not the way to go about it. Do you want to go have a nap? Or do you want to release some tension?” He offered, his initial angry tone shifting into something a little more seductive.

You couldn’t lie, his voice was a major turn on for you, and hearing his voice get gravelly and low definitely made the latter sound super appealing.

“Uhm. What did you have in mind?” You wondered out loud, while moving further into his room.

“heh. well for one, I think ya need to be taught a little lesson,” Red suggested, patting his lap for emphasis.

The excitement in your belly grew anxiously, this was good, you could definitely accept this. You laid down over his lap, and his hands were immediately on your rear, squeezing and groping. Contentment rippled through you, not unlike the feeling of a craving being satisfied. You enjoyed when he touched you.

Red lightly smacked one of your cheeks, the sting rippling throughout made you shimmy a little bit. He brought his hand down a little harder on the other cheek next, eliciting a gasp from you. You squirmed as the sting faded. He struck down again, this time both cheeks under his palm. You let out a quiet moan and squirmed a little more, heat beginning to pool in your abdomen.

“Pants off,“ Red growled, hoisting you upright. 

You obeyed, and watched him pull out a large rolling case from his closet. The butterflies in your stomach feeling as large as bats, you observed as he opened it. Inside the case were various paddles, crops and floggers, but you’d seen some of them before. He grabbed out two paddles, one small one large, and held them up to you. 

“Green,” you smiled, and he pointed to the bed. 

You did as you were told, bending over the bed so your bum was upright. 

You waited a couple moments, and looked over your shoulder at Red. He was just standing there, observing you, the flush obvious on his face. It looked like he was deep in thought though, so you shimmied your hips to get his attention again. 

You were rewarded with a loud smack and the beautiful stinging sensation of his bone hand on your bare ass. 

“Unf! Yes Daddy!” You called out before you could stop yourself, feeling slightly mortified at your accidental slip up (dang all those tiktoks). 

You glanced over your shoulder to see Red’s face super flushed, his grip on the smaller paddle tight. You weren’t sure what to do, until then suddenly he was right next to you, grabbing your hair and growling in your ear.

“Do ya like calling me Daddy? Because I’ll be your Daddy if ya want, naughty little one. I know ya enjoy me spanking ya, ya probably woke me up on purpose. Tch. You’re just lucky I love the sight of your bare ass, all warmed up...” he emphasized, squeezing your bare asscheeks. 

You couldn’t help but moan, arching your butt into his hand.He stood up and stepped away, chuckling low. You felt the bite of the smaller paddle as you heard it, with a resounding thwack. You groaned, and bit down on your arm, in an attempt to muffle your cries. 

Thwack! On your other cheek this time, the sting only heightening your anticipation. 

Thwack! The bedsheets under you were becoming damp from your arousal. 

“Harder Daddy,” you moaned, squirming around some more.

“Stay. Still.” Red growled, as he switched up the paddle to the larger heavier one. 

Your eyes rolled back in anticipation, and you grabbed a nearby pillow to bite down on. 

“Colour?” He asked softly, gently massaging your buttcheeks.

“Very much Green,” you inhaled.

Your rear burst into delightful stinging as the paddle made impact, causing you to cry out into the pillow. 

The next impact caught you on your thighs, the unexpected bite of the paddle causing you to cry out. The sensation of blood flow chasing the sting only added to your building pleasure. 

Red swung again, just as you arched your rear into the air. You could feel the sting on more than just your ass and the coil inside you snapped tight.

You quickly got on all fours, motioning to Red to come to you. 

“Please Daddy... I need to come...” you begged him.

“Fuckin hell little one look at ya... begging for me to help ya.”

He freed his hard cock from his shorts, the girth still as impressive as always. He prepped you, and pushed inside your hole slowly, almost agonizingly. You impatiently pushed down on him, desperately needing to be fucked. He groaned and chuckled, catching the hint.

He pumped into you hard and fast, as you stroked yourself fast, chasing your climax.   


“That’s it little one, come for Daddy” he groaned, squeezing and massaging your hips and ass.

You focused on the throbbing ache in your ass cheeks and exploded into your orgasm, gushing onto the bedsheets. Red wasn’t too far behind, coming inside you, making you shake in overstimulation. The two of you collapsed into a sweaty pile, cuddling close and dozing off.

When you woke, you noticed on the nightstand there was a glass of water for you with a couple of monster candies. A note read ‘just in case. xo’

Before nodding off again you noticed a couple baskets of clean folded laundry. 


	15. MASSIVELY BEHIND

**Summary for the Chapter:**

> Not an actual chapter, will delete and replace when ready.

I am still writing these, I wanna make that 100% clear. I’ve started a few more on the list but can’t seem to make my way through them, I’m exhausted, the characters aren’t speaking to me, or even just I feel like a broken record. Also kinda unmotivated? Obviously kink and sex is way more than reaching climax but I’m also trying to remember this is smut with fictional skeletons not real life lmao

anyway. I will get through them, moving with kids is just overwhelming.

if you’re still here- thank you🖤 maybe leave me a comment on your fave chapter so far if you haven’t already? 🌙 Happy Halloween lovelies

**Author's Note:**

> Undertale belongs to Toby Fox  
> Undertail is the deemed appropriate smut tag


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